Steviol

Base Information

• Chemical Name: Steviol
• CAS No.: 471-80-7
• Deprecated CAS: 13095-77-7,4574-62-3
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Hs Code.: 29181990
• UNII: 4741LYX6RT
• DSSTox Substance ID: DTXSID50897427
• Nikkaji Number: J9.989I
• Wikipedia: Steviol
• Wikidata: Q426852
• RXCUI: 1363645
• Metabolomics Workbench ID: 47463
• ChEMBL ID: CHEMBL463996
• Mol file: 471-80-7.mol

Synonyms:steviol;steviol, (+,-)-isomer;steviol, 3H-labeled

Chemical Property of Steviol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 215°
• Refractive Index: 1.569
• Boiling Point: 464.5 °C at 760 mmHg
• PKA: 4.65±0.60(Predicted)
• Flash Point: 248.8 °C
• PSA: 57.53000
• Density: 1.17 g/cm³
• LogP: 4.15500
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 583

Purity/Quality:

≥98% ^*data from raw suppliers

Steviol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)O)(C)C(=O)O
• Isomeric SMILES: C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@](C3)(C(=C)C4)O)(C)C(=O)O
• Uses: Has been proposed as non-nutritive sweetening agent. Steviol is an aglycone of the natural sweetener Stevioside (90%, S686730) and is found to be highly mutagenic compared to Stevioside.

Technology Process of Steviol

There total 7 articles about Steviol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.84%

stevioside (57817-89-7) → β-D-glucose (492-61-5) + steviol (29584-19-8,471-80-7)

Guidance literature:

With water; at 80 ℃; for 36h; Reagent/catalyst; chemospecific reaction; Enzymatic reaction;

DOI:10.1016/j.molcatb.2014.03.011

Reference yield:

stevioside (57817-89-7) → 13-hydroxy-ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester (1185737-16-9) + β-D-glucose (492-61-5) + steviol (29584-19-8,471-80-7) + 13-O-β-D-glucopyranosyl-19-O-β-D-glucopyranosylsteviol (64849-39-4,104873-42-9)

Guidance literature:

With β-galactosidase from Sulfolobus solfataricus; water; at 85 ℃; for 3h; Reagent/catalyst; chemospecific reaction; Enzymatic reaction;

DOI:10.1016/j.molcatb.2014.03.011

Reference yield:

C43H68O22 (1326217-31-5) → D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + D-Glucose (2280-44-6) + steviol (29584-19-8,471-80-7)

Guidance literature:

With sulfuric acid; In methanol; for 8h; Reflux;

DOI:10.1016/j.phytol.2011.01.002

upstream raw materials:

stevioside

C₄₃H₆₈O₂₂

stevioside

rebaudioside A

Downstream raw materials:

isosteviol

13-hydroxy-ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester

Refernces

• 1、 Perera, Wilmer H.,Docampo, Maite L.,Wiggers, Frank T.,Hufford, Charles D.,Fronczek, Frank R.,Avula, Bharathi,Khan, Ikhlas A.,McChesney, James D.. "Endocyclic double bond isomers and by-products from rebaudioside A and stevioside formed under acid conditions". . p. 163 - 170. Retrieved 2018/04/20.
• 2、 Wan, Hui-Da,Tao, Guan-Jun,Kim, Doman,Xia, Yong-Mei. "Enzymatic preparation of a natural sweetener rubusoside from specific hydrolysis of stevioside with β-galactosidase from Aspergillus sp.". experimental part. p. 12 - 17. Retrieved 2012/10/08.